Lucifer yellow: Difference between revisions

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Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (
 
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{{orphan|date=June 2010}}

{{Chembox
{{Chembox
| Verifiedfields = changed
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| verifiedrevid = 408230839
| Watchedfields = changed
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| ImageFile = Lucifer yellow.png
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| verifiedrevid = 410367079
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| ImageSize = 250px
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| ImageFile = Lucifer yellow.svg
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| IUPACName = 6-amino-2-(hydrazinecarbonyl)-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonate de dilithium
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| ImageSize = 200px
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| Section1 = {{Chembox Identifiers
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| PIN = Dilithium 6-amino-2-(hydrazinecarbonyl)-1,3-dioxo-2,3-dihydro-1''H''-benzo[''de'']isoquinoline-5,8-disulfonate
| CAS = {{CAS|7|7|9|4|4|8|8|8}}
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|Section1={{Chembox Identifiers
| CASNo = 77944-88-8
| CASNo_Ref = {{Cascite|changed|CAS}}
| PubChem = 20835957
| PubChem = 20835957
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 52104
| ChEBI = 52104
| ChEMBL = 1650069
| UNII = 9654F8OVKE
| SMILES = c1c(cc2c3c1c(c(cc3c(=O)n(c2=O)C(=O)NN)S(=O)(=O)[O-])N)S(=O)(=O)[O-].[Li+].[Li+]
| SMILES = c1c(cc2c3c1c(c(cc3c(=O)n(c2=O)C(=O)NN)S(=O)(=O)[O-])N)S(=O)(=O)[O-].[Li+].[Li+]
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
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| InChI = 1S/C13H10N4O9S2.2Li/c14-10-5-1-4(27(21,22)23)2-6-9(5)7(3-8(10)28(24,25)26)12(19)17(11(6)18)13(20)16-15;;/h1-3H,14-15H2,(H,16,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2 }}
| ChemSpiderID = 20137740
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| Section2 = {{Chembox Properties
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
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| formula = |C=13|H=10|N=4|O=9|S=2|Li=2
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| StdInChI = 1S/C13H10N4O9S2.2Li/c14-10-5-1-4(27(21,22)23)2-6-9(5)7(3-8(10)28(24,25)26)12(19)17(11(6)18)13(20)16-15;;/h1-3H,14-15H2,(H,16,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2
| MolarMass = }}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DLBFLQKQABVKGT-UHFFFAOYSA-L
}}
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|Section2={{Chembox Properties
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| C=13 | H=10 | Li=2 | N=4 | O=9 | S=2
}}
}}
}}


'''Lucifer yellow''' is a fluorescent dye used in [[cell biology]]. The key property of Lucifer yellow is that it can readily visualized in both living and fixed cells using a [[fluorescence microscope]]. Lucifer yellow was engineered by [[Walter W. Stewart]] at [[NIH]] and patented in 1978.<ref>[http://www.freepatentsonline.com/4473693.html Patent description]</ref>
'''Lucifer yellow''' is a [[fluorophore|fluorescent dye]] used in [[cell biology]].<ref>{{cite journal|last=Hanani|first=Menachem|title=Lucifer yellow – an angel rather than the devil|journal=Journal of Cellular and Molecular Medicine|date=January 2012|volume=16|issue=2|pages=22–31|doi=10.1111/j.1582-4934.2011.01378.x|pmid=21740513|pmc=3823090}}</ref> The key property of Lucifer yellow is that it can be readily visualized in both living and fixed cells using a [[fluorescence microscope]]. Lucifer yellow was invented by Walter W. Stewart at the [[National Institutes of Health]] and patented in 1978.<ref>[http://www.freepatentsonline.com/4473693.html Patent description]</ref>


== Preparations ==
== Preparations ==
For common usage it is compounded with [[carbohydrazide]] (CH) and prepared as a [[Lithium]] salt. The CH group allows it to be [[covalent]]ly linked to surrounding biomolecules during [[aldehyde]] fixation.
For common usage it is compounded with [[carbohydrazide]] (CH) and prepared as a [[lithium]] [[salt (chemistry)|salt]]. The CH group allows it to be [[covalent]]ly linked to surrounding biomolecules during [[aldehyde]] [[fixation (histology)|fixation]].<ref>{{cite web|title=Lucifer Yellow CH, Lithium Salt|url=http://www.lifetechnologies.com/order/catalog/product/L453|work=Molecular Probes|accessdate=17 March 2014}}</ref>


Other [[cation]]s such as [[ammonium]] or [[potassium]] can be used when lithium is undesirable, but the resulting salts are less soluble in water.
Other [[cation]]s such as [[ammonium]] or [[potassium]] can be used when lithium is undesirable, but the resulting salts are less soluble in water.


Lucifer yellow can also be compounded as a [[vinyl]] [[sulfone]], with [[ethylenediamine]], or with [[cadaverine]].
Lucifer yellow can also be compounded as a [[Vinyl group|vinyl]] [[sulfone]], with [[ethylenediamine]], or with [[cadaverine]]. {{what|date=January 2016}}


== References ==
== References ==
<references/>
<references/>

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* [http://probes.invitrogen.com/media/pis/mp00453.pdf Invitrogen's manual for Lucifer yellow]
==External links==
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* [https://web.archive.org/web/20110516164133/http://probes.invitrogen.com/media/pis/mp00453.pdf Invitrogen's manual for Lucifer yellow]
* [http://omlc.ogi.edu/spectra/PhotochemCAD/html/luciferyellowCH.html Molecular structure and spectra of Lucifer yellow CH (lithium salt)]
* [http://omlc.ogi.edu/spectra/PhotochemCAD/html/luciferyellowCH.html Molecular structure and spectra of Lucifer yellow CH (lithium salt)]







{{science-stub}}

[[fr:Jaune lucifer]]
[[Category:Fluorescent dyes]]
[[Category:Fluorescent dyes]]
[[Category:Hydrazides]]
[[Category:Sulfonates]]
[[Category:Heterocyclic compounds with 3 rings]]
[[Category:Nitrogen heterocycles]]
[[Category:Lithium compounds]]
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